Design, synthesis, and preliminary pharmacological evaluation of novel thiazolidinone derivatives as potential benzodiazepine agonists

Almasirad, Ali; Maryam, Ghadimi; Mirahmadi, Saeideh; Kodakan, Pouya Ahmadian; Jahani, Reza; Nazari, Maryam; Rezaee, Elham; Azizian, Homa; Rabizadeh, Parmida; Tabatabai, Sayyed Abbas; Faizi, Mehrdad

doi:10.1007/s11030-021-10182-x

Cited by 7 publications

(4 citation statements)

References 25 publications

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“…Compound 158 as novel benzodiazepine agonist showed appropriate sedative-hypnotic activity, potent anticonvulsant activity, reduced memory impairment and no muscle relaxant influence in vivo assays. The ED50 values were 12.97 mg/kg (maximal electroshock seizures), 15.94 mg/kg (pentabarbital-induced sleeping test) and 21.07 kg/mg (openfield test) [155].…”

Section: Cerebrovascular Protection Activity and Properties Against Neurological Disordersmentioning

confidence: 98%

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mech

Kurowska

Trotsko

2021

IJMS

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Thiazolidin-4-ones is an important heterocyclic ring system of a pharmacophore and a privileged scaffold in medicinal chemistry. This review is focused on the latest scientific reports regarding biological activities of thiazolidin-4-ones published in 2020 and 2021. The review covers recent information about antioxidant, anticancer, anti-inflammatory, analgesic, anticonvulsant, antidiabetic, antiparasitic, antimicrobial, antitubercular and antiviral properties of thiazolidin-4-ones. Additionally, the influence of different substituents in molecules on their biological activity was discussed in this paper. Thus, this study may help to optimize the structure of thiazolidin-4-one derivatives as more efficient drug agents. Presented information may be used as a practical hint for rational design of new small molecules with biological activity, especially among thiazolidin-4-ones.

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Section: Cerebrovascular Protection Activity and Properties Against Neurological Disordersmentioning

confidence: 98%

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mech

Kurowska

Trotsko

2021

IJMS

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“… 20 4-Chloro-2-(2-fluorophenoxy)- N -(4-oxo-2-( p -tolyl)thiazolidin-3-yl)benzamide exhibited considerable benzodiazepine agonists, possessing anticonvulsant effects. 21 Thiazolidinone-based compounds were proved to be promising drugs and acted as single-targeted and multi-targeted agents for controlling hyperglycemia in patients suffering from type 2 diabetes mellitus (DM) and associated complications by evaluating their inhibitory effects against PPA and α-glucosidase.…”

Section: Introductionmentioning

confidence: 99%

“…An innovative series of 5-benzylidene-2-arylimino-4-thiazolidinone derivatives consisting of a phenylaminopyrimidine core were tested for their anticancer activity on K562 (chronic myeloid leukemia), PC3 (prostate cancer), and SHSY-5Y (neuroblastoma) cells . 4-Chloro-2-(2-fluorophenoxy)- N -(4-oxo-2-( p -tolyl)thiazolidin-3-yl)benzamide exhibited considerable benzodiazepine agonists, possessing anticonvulsant effects . Thiazolidinone-based compounds were proved to be promising drugs and acted as single-targeted and multi-targeted agents for controlling hyperglycemia in patients suffering from type 2 diabetes mellitus (DM) and associated complications by evaluating their inhibitory effects against PPA and α-glucosidase.…”

Section: Introductionmentioning

confidence: 99%

Mercaptobenzimidazole-Based 1,3-Thaizolidin-4-ones as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, and Molecular Docking Studies

et al. 2022

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In this research work, we have focused our efforts to synthesize a series of 2-mercaptobenzimidazole-based 1,3-thiazolidin-4-ones ( 5–24 ) following a multistep reaction strategy and characterization of the synthesized derivatives with the help of various spectroscopic techniques. To find the antidiabetic potentials of the synthesized compounds ( 5–24 ), in vitro alpha-glucosidase inhibitory activity was performed using acarbose (IC 50 = 873 ± 1.2 μM) as the reference standard. The results of the antidiabetic assay were very encouraging because compounds 5 , 8 , and 14 showed excellent inhibitions with IC 50 values of 5.22 ± 0.14, 5.69 ± 0.10, and 10.20 ± 0.12 μM, respectively. The experimental results of anti-alpha-glucosidase activity prompted us to investigate and propose a possible mechanism of how the active molecules will interact with the target enzyme. For this purpose, molecular docking with the AutoDock Vina (an open-source and reliable docking platform) gave us an insight into the binding interactions of the active compounds to different amino acid residues of the enzyme.

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“…Thiazolidinone ring is a promising pharmacophore that has possessed a broad spectrum of pharmacological actions such as antimicrobial (compound A) (Fig. 1 ) [ 3 – 5 ], antiviral [ 6 ], antiparasitic [ 7 , 8 ], analgesic, anti-inflammatory [ 9 ], antioxidant [ 10 ], anticancer [ 6 , 7 , 11 ], antidiabetic [ 12 ], antihypertensive, anti-hyperlipidemic, anti-arrhythmic [ 13 ], anti-convulsant activities [ 14 , 15 ]. In the last two decades, 4-thiazolidinone pharmacophore has received great attention for its inhibitory effect on MurB and various substituted 4-thiazolidinones were explored for their antibacterial activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one derivatives as anti-MRSA and anti-H. pylori agents

et al. 2022

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In this work, we have synthesized twenty five new 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one derivatives bearing an aryl or heteroaryl methylene group on position 5 of thiazolidinone and evaluated their antimicrobial activity against Gram-positive and -negative bacteria as well as three metronidazole resistant Helicobacter pylori strains. Most of the compounds were very potent towards tested Gram-positive bacteria and showed an antibacterial efficacy substantially greater than ampicillin as the reference drug. However, no effectiveness was observed for the Gram-negative microorganisms. The compounds 9, 20 and 29 exhibited strong antimicrobial activity against Helicobacter pylori strains (inhibition zone > 30 mm) in 100 μg/disc and (inhibition zone > 20 mm) in 50 μg/disc. Taking these findings together, it seems that these potent antibacterial derivatives could be considered as promising agents for developing new anti-infectious drugs against microorganisms resistant to currently available antibiotics. Graphical Abstract

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Design, synthesis, and preliminary pharmacological evaluation of novel thiazolidinone derivatives as potential benzodiazepine agonists

Cited by 7 publications

References 25 publications

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

The Bioactivity of Thiazolidin-4-Ones: A Short Review of the Most Recent Studies

Mercaptobenzimidazole-Based 1,3-Thaizolidin-4-ones as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, and Molecular Docking Studies

Synthesis of new 2-(5-(5-nitrofuran-2-yl)-1,3,4-thiadiazol-2-ylimino)thiazolidin-4-one derivatives as anti-MRSA and anti-H. pylori agents

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